You’re struggling with how to start an email to someone you’ve never met (about something you don’t really care about), so you ask your ever-ready AI assistant for help on the draft. The draft email is surprisingly good. Maybe it doesn’t sound like you, but a stranger wouldn’t know or care about that, so you fire it off as-is. Good enough.

The recipient emails you back within minutes with the information you need, which is electrifying. You’re sure he had no idea you used AI. And so what if he did? You repeat the trick for a few more emails that day—this time with people you know—and a mild euphoria replaces the late afternoon energy dip. Maybe there’s something to the AI hysteria, after all.

The next morning, you’ve had a crummy night’s sleep after a failed round of sleep training for your youngest (your husband always caves), and you’re not sure this morning’s matcha latte contains any of the chemicals that got you through grad school. Your eyes glaze over as your inbox does its best impression of infinity.

So you give in and let AI access your inbox. By the time you launch Zoom for your first meeting, you have draft responses for all the emails in your inbox, with 4 flagged for your attention. Not bad.

After a few days of trusting AI to email people on your behalf—admittedly something you were strongly opposed to last month—you’re now free to tackle your backlog of actual work. You know, the reports, presentations, and summaries that AI is more than capable of helping you with…

And with the email context it now has, the drafts you ask AI for are surprisingly good. And why not? Your colleagues are using it, too. You have a strong week.

By the end of the week, you’re drunk with (AI) power and thanks to some onboarding videos at work—okay, you skimmed the AI-generated summaries of the videos, fine— you’re using it for weekend itineraries, dinner recipes, and travel planning. This buys you a bit of downtime since you’ve cleverly built some entertainment for the kids into the weekend.

Now you can deploy AI on your creative projects, which is the ultimate goal. You don’t just want productivity for its own sake; you want to spend less time doing tasks that deplete you, and more time doing creative work that energizes you.

Sunday rolls around, as it often does, and you’re in a full-blown AI psychosis. You’re determined to have the most optimized week in human history, so you take a peek at your work inbox to get a head start on crafting an even better round of AI-generated responses to the AI-drafted emails from last week.

You feel a pang of inexplicable despair, but this gives way to a sense of accomplishment when your inbox transforms from chaos to completion.

You’re running behind on Monday morning and start your first call from the car, annoyed that your company has backslid on its commitment to the hybrid workplace you signed up for.

You set down your bag, open your laptop, check your Outlook, and start to cry.

My friend Jason is an entrepreneur, attorney, and former Obama White House staffer who beautifully captured his upbringing in rural Maryland in a memoir about what it means to have deep roots in a place that, over time, grows unrecognizable branches.

Clarity, Community, and Creation are the central tenets of Next Year Starts Now, and here’s why I prioritized these over the dozen or so that I could have.

Clarity is table stakes. Without it, any path can seem viable. There’s a time and place for experimentation and improvisation, but a clear direction and vision for success is what keeps you from returning to the path.

Community creates accountability. You might not feel like showing up for yourself every day, but in showing up for others, you can find yourself renewed and reinvigorated. The right conversation with the right person at the right time can change your life, and community helps create more surface area for serendipity.

Creation is where the real transformation takes place. I love vision boards, intentions, and affirmations, but the unglamorous commitment to doing the work is what allows our dreams to take flight. We start before we’re ready, trust the process, and above all, we ship.

Next Year Starts Now 🚀

Eight years after meeting one of my best friends, I found out he was a classically trained pianist whose first love is music. His passion runs so deep that he swore off picking up the keys until he retires, because it’s so consuming.

I didn’t even learn this trivia directly—he shared it with the friend of a mutual friend when we were all hanging out one evening in Portugal. I looked at him like he had grown horns, but I shouldn’t have been surprised.

New connections create the space for us to show up in ways that break us out of our typical scripts and patterns. The people I speak with most frequently are familiar with the things I care about, but not the person I made small talk with on an elevator yesterday or the barista who asks me how my day is going.

When we spend time with people whose lives and careers differ from our own, we discover the familiar and the foreign. The familiarity can be affirming when we feel like someone we’ve never met sees the world similarly. And the foreignness of their approach to problem-solving or to asking us about ourselves can yield insights and reflections that stay with us for years.

I look forward to amplifying this magic in Next Year Starts Now 🚀. The people who have signed up don’t know each other, and they’re all extremely accomplished in their respective fields. And even if I don’t have the pleasure of seeing you in the program, I hope you’ll share and learn something new this week.

Next Year Starts Now 🚀

Do you trust yourself? A lot of people don’t.

One of the reasons for the self-doubt people feel when trying to change a behavior or start a new habit is that sustained change is hard. Did you know that nearly 80% of New Year’s resolutions are abandoned by the second week of February?

One challenge is that we approach change from a behavioral perspective without addressing the identity gap. If your goal of working out four times a week started strong but fell off after a long weekend or a friend visiting town, it’s not just because you aren’t committed. It’s because the new identity hasn’t been fully internalized.

If you instead started with doing five air squats while waiting for your kettle to heat up in the morning—a durable habit less susceptible to interruption given the context—you can much more easily build upon this habit with more activities that eventually spill over into the gym or onto the running trail.

And after twenty or thirty days of this, the habit starts becoming automatic. After months of this, it’s hard not to see yourself as a person who prioritizes fitness because the evidence is clear.

(Put another way, caffeine addicts coffee drinkers don’t have to summon the willpower to swing by their favorite coffee shop once they’ve found it, much less do they need to put time on their calendar to remember. It’s who they are.)

This applies to aspiring writers, programmers, or mindfulness practitioners. You might not have time to publish a thousand words, code an error-handling module, or sit on a cushion for 30 minutes every morning. But I don’t know anyone who doesn’t have time to pen one sentence, write a single line, or breathe for 30 seconds.

After a while, the identity of who you’re becoming gets assimilated. You move from “how could I possibly make time?” to the day not feeling right if you haven’t done the thing to which you’ve committed.

In Next Year Starts Now 🚀, we close the gap between the person we’re becoming and the person we are today. We have a bias for action, we start before we’re ready, and we’re doing the work.

Next Year Starts Now 🚀

In 2015, I moved to NYC, founded a media company, and became Seth Godin’s in-house CTO. But my hesitation almost prevented it from happening.

At the time, I was Director of Web Optimization for a firm that made software used by more than a million websites. I was running professional services and learning a lot, but something felt off. I couldn’t shake the feeling that it was time for a new adventure.

I emailed Seth, who had previously hired me for his book publishing startup called The Domino Project, and told him I was thinking about my next moves. He responded 19 minutes later, asking me to call him. We talked about what I wanted to do next, what it would look like, what he was preparing to launch, and the role I could play.

I was living in Florida at the time, and he suggested that we continue the conversation in person, in New York. I hemmed and hawed about the next time I’d be in New York, to which he replied, “I’m not waiting.”

I booked my flight that day and moved to Harlem a few weeks later.

Things moved quickly. I secured sponsors. Helped launch altMBA. Cultivated contributors. Hired an Editor-in-Chief. Published articles. Grew the newsletter. Produced a launch event. Made a name for myself.

I learned more in those first two weeks than I would have in two years of puttering along in Florida. It had nothing to do with where I lived and everything to do with how I chose to spend my time. I left the safety of the familiar and stepped into the unknown. It was thrilling.

And none of it would’ve happened if I had dragged my feet.

The problem with waiting is that there’s never an ideal or convenient time to do the work we’re called to do. There will always be great reasons to postpone, delay, and spend another six months “researching.”

That’s why I’m launching Next Year Starts Now 🚀.

It’s an invitation, a permission slip, and a mirror for you to hold yourself accountable. There’s still time to close the year out strong.

Next Year Starts Now 🚀

You don’t have to wait for the New Year to get started on your resolutions. In fact, I’d argue that waiting for January 1st is the worst way to make a change.

Did you know that of the 41% of Americans who make New Year’s resolutions, only 9% are successful in keeping them?

We can do better than that.

You don’t have to be great to start, but you do have to start to be great. — Zig Ziglar

As the end of the year comes into focus and the holiday season approaches, a growing list of our nice-to-have priorities will be punted to the “next year” pile. And when the fog of the new year clears and the urgency of those punted priorities comes into focus, abandoning our goals and resolutions is the easiest way to make time.

But your dreams deserve better.

The truth is that right now is always the best time to make a change, but right now is never convenient. In fact, the inconvenience of deciding, committing, and taking immediate action is what’s transformative. I know this because taking immediate action—the core of my Next Year Starts Now ethos—changed my life.

Right now prevents us from hiding, demonstrates (most importantly, to ourselves) how serious we are, and interrupts the time-honored tradition of getting ready to get ready, a pattern that kept me stuck and living below my potential for years.

So in that spirit, I hope you’ll consider joining me for an intentionally inconvenient end-of-year sprint. Registration will be open for two weeks starting today, and I hope to see you inside. Email me with any questions.

LFG 🚀

I frequently walk through an intersection in Brooklyn where cars are occasionally stopped in the middle of the pedestrian walkway. It’s a minor inconvenience to walk around the bad drivers who misjudge the intersection, but it’s still difficult not to feel a twinge of annoyance.

But when I was returning a rental car a few months ago, I found myself traveling through this same area in a vehicle for the first time. The light was yellow and there were lots of pedestrians, so I decided to stop instead of trying to make the light.

I had to smile as a couple walked a few paces out of their way to accommodate the bad driver—yours truly—whose turn it was to inconvenience pedestrians.

The funny thing about extending grace is that it flows in both directions. You might not need it today, but life is long and filled with surprises.

I love tools that make the internet a more private and secure place, and here are a few products and services that I use. Many of them will be overkill for the average consumer, but you might not be the average consumer.

• NextDNS: Cloud-based DNS service that lets you control and monitor DNS resolution on your devices with a focus on privacy, security, and content filtering. Blocks ads, trackers, and prevents your ISP from snooping on your DNS traffic.
• 1.1.1.1: CloudFlare’s super-fast, privacy-respecting DNS resolver that doesn’t log or track your browsing activity. There’s also a companion mobile app that works like a VPN and securely connects to the Cloudflare network.
• Flashrouters: Wi-Fi routers that come with open-source and highly customizable software installed, allowing you to enjoy an expanded feature set, better security, and improved performance. I run an Asus mesh network at home.
• Tailscale: A secure networking tool that creates a private, encrypted network between your devices. Works like a VPN, and uses the Wireguard protocol.
• Proton: Suite of high-quality, privacy-focused tools created by former CERN scientists. Their mail, VPN, password manager, and secure notes app are top-notch.
• Brave: Free, privacy-focused web browser based on Chromium (which powers Google Chrome) that blocks ads by default.
• Ente Photos: End-to-end encrypted, open-source, cross-platform photo backups.
• Signal: Secure, end-to-end encrypted messaging. SMS is not secure.
• Advanced Data Protection for iCloud: An optional security feature from Apple that gives you end-to-end encryption for your iCloud data.